Borneol


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borneol

[′bȯr·nē‚ȯl]
(organic chemistry)
C10H17OH White lumps with camphor odor; insoluble in water, soluble in alcohol; melting point 203°C; used in perfumes, medicine, and chemical synthesis.

Borneol

 

bornyl alcohol, a secondary alcohol of the bicyclic terpene group. Borneol has an endo configuration; its isomer, called isoborneol, has an exo configuration. [The (CH3)2C group is located outside the plane of the ring.]

Borneol and isoborneol contain an asymmetric carbon atom (denoted by an asterisk), and therefore each of them exists in two optically active forms and one inactive racemic form (−, +, and ±). Borneo camphor, (+)-borneol, is contained in the secretions of the tree Dryobanalops camphora, which grows on the islands of Borneo and Sumatra, as well as in rosemary, lavender, and camphor oils. The acetate form, ( − )-borneol, is contained in the coniferous needle of the Siberian pine. Both (+)-borneol and (−)-borneol have a melting point Tm = 208.5° C, boiling point Tb = 212° C, and angle of rotation of the plane of polarization [α]D20 = ±37.9°; and both sublimate. The racemate (±)-borneol melts at 210.3° C. Both (−)-borneol and (±)-borneol are components of valerian oil.

Borneol is converted into camphor upon oxidation and catalytic dehydrogenation; the dehydration of borneol leads to camphene. The primary method of obtaining borneol is the hydration of pinene, which is contained in turpentine. Borneol is used in the production of camphor.

Isoborneol (Tm= 214° C) is not found in nature; it is obtained from camphene.

References in periodicals archive ?
The capacity of our major products is: 15000 MT of gum rosin, 12000 MT of rosin ester, 2000 MT of gum turpentine and 300 MT of Borneol, with an owned forest with an 3300 hectares.
Detected VOCs were pentanal, hexanal, [alpha]-pinene, [beta]-pinene, octanal, heptane, borneol, heptadecane, and octadecane.
6,232,341 B1: Researchers for Hedonist Biochemical Technology, Taipei, Taiwan, have patented a topical pharmaceutical composition with borneol and bismuth subgallate to prevent skin scarring and granulation.
Along with the fast development of China's gum turpentine derivatives, the overseas enterprises tend to purchase Chinese-made gum turpentine derivatives (such as synthetic camphor, terpineol, synthetic borneol, etc.
In addition to these, other monoterpenes such as borneol, bornyl acetate, and isoborneol, 1,8-cineole, thujone, and camphor exhibited considerable antiviral activities against HSV-1 (Dunkic et al.
13, 14] reported the 1,8cineole, [alpha]-thujone, [beta]-thujone, borneol and camphor were the major compounds found in the sage essential oils.
They include organic acids (acetic, benzoic, cinnamic and phenylacetic); alcohols (benzyl alcohol, borneol, cinnamyl alcohol, citronellol, geraniol, linalool, menthol, phenylethyl alcohol and terpineol); aldehydes (anisic aldehyde, cinnamic aldehyde, benzaldehyde, citral, piperonal or heliotropin, salicylic aldehyde and vanillin); ketones (carvones, camphor, thujone, pulegone, etc; esters such as bornyl acetate, methyl salicylate, benzyl benzoate, geranyl acetate and linalyl acetate); phenols (thymol, carvacrol and chavicol); phenol ethers (anethol, eugenol and safrol) and many other more complex compounds such as coumarin and indol.
In China, pinene is mainly applied in dihydromyrcene/dihydromyrcenol, synthetic camphor, synthetic borneol and all kinds of synthetic perfume.
2-3 List of major synthetic borneol producers in China, 2012
In this research Kamfr, 1,8-cineol, borneol and myrtnvl were identified as major compounds [12].
The chemicals used in this study for the collection and analysis of VOCs were methylene chloride, formaldehyde, methanol, formic acid, acetic acid, propionic acid, butyric acid, hexanal, [alpha]-pinene, [beta]-pinene, octanal, D-limonene, borneol, naphthalene, hexadecane, heptadecane, and octadecane.